I have done this often, and each time made modifications to the system. I will preface with the following equipment
on board my boat:
2 spare halyards
4 spare snatch blocks
2-1/2" diameter spinnaker pole
11' AB inflatable
with 25 HP Yamaha
16 gallon fuel tank
I use one halyard
as a topping lift
to the outer pole end. (my pole attaches to the mast
track ball and socket and has a hand winch
with continuous line that raises it to vertical and latches
to the mast when not in use) The important thing here is to set the pole at a level high enough so you don't have to raise it during the process of hoisting.
I run a line tied to the outer tip of the pole to a block attached to the other end which is measured to be centered over the ring of the hoisting bridal. I then run the second halyard thru the block and attach the halyard shackle to the bridal ring. This allow me to hoist straight up from the chock. The pole is actually not taking the boat weight which is around 800 pounds, the halyard is doing the work.
I have a spare line that is 30 feet long that I actually run thru the centering block on the pole to the halyard itself and it gives me enough tail on the halyard to run thru a snatch block that is on a pad eye used to secure the baby stay on the outboard
rail. Then the halyard is led back to the electric
The final step is to take another spare line tied to the pole tip that leads back to the unused primary winch. This line swings the pole outboard
with control and compensates for the issue caused by heeling of the boat. Once the boat is outboard and clear of the shrouds,
I square the boat up with the dingy mooring
lines by tying them to the lifeline on the boat. I then start easing the boat down with the halyard on the primary winch.
It takes about 15 to 20 minutes to load or offload the dingy with this method and I have done it by myself. I prefer to have one other hand to assist with keeping the dingy pushed off the boat which is navy
blue and will show white scuffs every time the dingy rubs it going up or down.